4-Methoxyphenyl 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyanoside

Base Information

• Chemical Name: 4-Methoxyphenyl 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyanoside
• CAS No.: 14581-81-8
• Molecular Formula: C₂₁H₂₆O₁₁
• Molecular Weight: 454.431
• Hs Code.: 29389090
• DSSTox Substance ID: DTXSID40452842
• Nikkaji Number: J789.131H
• Wikidata: Q72517995
• Mol file: 14581-81-8.mol

Synonyms:14581-81-8;4-Methoxyphenyl 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyanoside;4-Methoxyphenyl 2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside;(2R,3R,4S,5R,6S)-2-(Acetoxymethyl)-6-(4-methoxyphenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate;[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(4-methoxyphenoxy)oxan-2-yl]methyl acetate;b-D-Glucopyranoside,4-methoxyphenyl, 2,3,4,6-tetraacetate;SCHEMBL4182294;DTXSID40452842;RPHXBVOPPUTUES-YMQHIKHWSA-N;4-Methoxyphenyl-2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside;AKOS015919161;CS-0198934;M1630;D91516;A808419;W-201284;Z1826957632;beta-D-Glucopyranoside, 4-methoxyphenyl, 2,3,4,6-tetraacetate;4-Methoxyphenyl 2-O,3-O,4-O,6-O-tetraacetyl-beta-D-glucopyranoside;[(2R,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-(4-methoxyphenoxy)oxan-2-yl]methyl acetate;(2R,3R,4S,5R,6S)-2-(Acetoxymethyl)-6-(4-methoxyphenoxy)tetrahydro-2H-pyran-3,4,5-triyltriacetate

Chemical Property of 4-Methoxyphenyl 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyanoside

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 102 °C
• Refractive Index: 1.523
• Boiling Point: 525.329 °C at 760 mmHg
• Flash Point: 225.706 °C
• PSA: 132.89000
• Density: 1.301 g/cm³
• LogP: 1.15710
• Storage Temp.: Freezer
• Solubility.: almost transparency in Chloroform
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 12
• Exact Mass: 454.14751164
• Heavy Atom Count: 32
• Complexity: 671

Purity/Quality:

98%, ^*data from raw suppliers

4-Methoxyphenyl 2,3,4,6-Tetra-O-acetyl-β-D-glucopyanoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OC2=CC=C(C=C2)OC)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC2=CC=C(C=C2)OC)OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of 4-Methoxyphenyl 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyanoside

There total 41 articles about 4-Methoxyphenyl 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyanoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2,3,4,6-tetra-O-acetyl-d-glucopyranosyl trichloroacetimidate (74808-10-9,86520-63-0,87119-53-7,92052-29-4,121238-27-5,127061-80-7,142831-80-9) + 4-methoxy-phenol (150-76-5) → p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (2872-65-3,14581-81-8,17042-40-9,84380-06-3,105260-62-6)

Guidance literature:

2,3,4,6-tetra-O-acetyl-d-glucopyranosyl trichloroacetimidate; 4-methoxy-phenol; In dichloromethane; at 0 ℃; Molecular sieve; Inert atmosphere;

With boron trifluoride diethyl etherate; In dichloromethane; for 3h; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.carres.2012.09.025

Reference yield: 99.0%

4-methoxy-phenol (150-76-5) + β-D-glucose pentaacetate (604-69-3) → p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (2872-65-3,14581-81-8,17042-40-9,84380-06-3,105260-62-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 16h; Inert atmosphere;

Reference yield: 98.0%

4-methoxy-phenol (150-76-5) + β-D-galactose peracetate (4163-60-4) → 4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (2872-65-3,14581-81-8,17042-40-9,84380-06-3,105260-62-6)

Guidance literature:

With boron trifluoride diethyl etherate; triethylamine; In dichloromethane; at 0 - 20 ℃; for 16h; Inert atmosphere;

DOI:10.1002/chem.201704379

upstream raw materials:

4-methoxy-phenol

β-D-glucose pentaacetate

(4-methoxyphenoxy)trimethylsilane

1-O-trimethylsilyl-2,3,4,6-tetra-O-acetyl-D-glucoside

Downstream raw materials:

p-methoxyphenyl 3-O-benzyl-β-D-galactopyranoside

4-methoxyphenyl 2,4,6-tri-O-acetyl-β-D-galactopyranoside

p-methoxyphenyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-galactopyranoside

p-methoxyphenyl 2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranoside

Refernces

• 1、 Bedini, Emiliano,Iadonisi, Alfonso,Silipo, Alba,Traboni, Serena,Vessella, Giulia. "Solvent-Free Glycosylation from per-O-Acylated Donors Catalyzed by Methanesulfonic Acid". . p. 5669 - 5676. Retrieved 2021/11/11.
• 2、 Chen, Xi,Diaz, Sandra,Kooner, Anoopjit Singh,Santra, Abhishek,Varki, Ajit,Yu, Hai. "Chemoenzymatic Synthesis of Sialosides Containing 7- N- or 7,9-Di- N-acetyl Sialic Acid as Stable O-Acetyl Analogues for Probing Sialic Acid-Binding Proteins". . p. 14381 - 14397. Retrieved 2021/11/01.